GB919720A - Hemi-acetals, their preparation and use - Google Patents

Hemi-acetals, their preparation and use

Info

Publication number
GB919720A
GB919720A GB25593/60A GB2559360A GB919720A GB 919720 A GB919720 A GB 919720A GB 25593/60 A GB25593/60 A GB 25593/60A GB 2559360 A GB2559360 A GB 2559360A GB 919720 A GB919720 A GB 919720A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
group
aldehyde
hydrogen
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB25593/60A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB919720A publication Critical patent/GB919720A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/47—Condensation polymers of aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B31/00—Preparation of derivatives of starch
    • C08B31/003—Crosslinking of starch
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C08G18/3209—Aliphatic aldehyde condensates and hydrogenation products thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/56—Polyacetals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C3/00—Tanning; Compositions for tanning
    • C14C3/02—Chemical tanning
    • C14C3/08—Chemical tanning by organic agents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/137—Acetals, e.g. formals, or ketals
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/06—Alcohols; Phenols; Ethers; Aldehydes; Ketones; Acetals; Ketals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/09—Polyolefin
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/10—Polyvinyl halide esters or alcohol fiber modification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Microbiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paper (AREA)

Abstract

Hemi-acetals of general formula <FORM:0919720/IV(a)/1> in which R is an alkylene radical, preferably containing 1-3 carbon atoms, x and y are integers of 1-5, n is an integer of at least 2 and R1 is a hydrogen or an alkyl group, at least one of the R1 groups being hydrogen, or alternatively two of the -OR1 groups may be removed and the remaining radicals joined together through an oxygen atom to form a cyclic structure or a carbonyl group, may be used to produce resinous materials. They may be reacted with polyhydric alcohols such as pentaerythritol, diand polypentaerythritols and the resulting product reacted with a polyisocyanate such as an arylene diisocyanate. Alternatively the hemiacetals may be reacted with phenols and the products subsequently reacted with epichlorohydrin in the presence of an alkali to form new epoxy resins.ALSO:Hydroxy-containing hemi-acetals are prepared by reacting under acidic conditions: (1) an aldehyde in which there is attached to the a - or b -carbon atom relative to the aldehyde group a hydroxyl, alkyl-sec.-amino-, primary amino or mercapto group, or an aliphatic carbon-carbon unsaturated linkage; and (2) a dissimilar aldehyde containing no reactive group other than the aldehyde group. Suitable aldehydes of type (1) are, for example, hydroxy adipaldehyde, hydroxy succinaldehyde, 2-hydroxy propionaldehyde, 3-hydroxy propionaldehyde, 3-aminopropionaldehyde, 2-hydroxy-butyraldehyde, 3-hydroxybutyraldehyde, 3-mercaptopropionaldehyde, 3-mercaptobutyraldehyde, 3 - aminopentanal, 3 - mercaptopentanal, 2-mercaptohexanal, 3-aminodecanal, 3-hydroxycyclohexanal, acrolein, methacrolein, crotonaldehyde, a -phenylacrolein, a -cyclohexyl-acrolein, 2-pentenal, 3-hexenal, 2-decenal, 2-cyclohexenal and 2-hydroxy-3-mercapto-tetradecanal. The preferred aldehyde of type (2) is formaldehyde and formaldehyde precursors such as formalin, paraformaldehyde, trioxane and methalal but other suitable aldehydes are acetaldehyde, butyraldehyde, pentanal, hexanal, octanal, dodecanal, cyclohexanal, 2,4-dimethyl-cyclohexanal, glyoxal, succinaldehyde, 1,8-octanedial, benzaldehyde, adipaldehyde and 3,5-diethylhexanal. The reaction is preferably carried out in the presence of water and/or one or more alcohols. The products of the process are hydroxy-containing hemi-acetals having the general formula <FORM:0919720/IV (b)/1> in which R is an alkylene radical, preferably containing 1-3 carbon atoms, x and y are integers of from 1 to 5, n is an integer of at least 2 and R1 is hydrogen or an alkyl group, at least one of the R1 groups being hydrogen; alternatively two of the -OR1 groups may be removed and the remaining radicals joined through an oxygen atom to form a cyclic structure or a carbonyl group. In addition there may be obtained small amounts of the following compounds:- <FORM:0919720/IV (b)/2> in which R is an alkylene radical, x is 1-5, and n is at least 2.
GB25593/60A 1959-07-24 1960-07-22 Hemi-acetals, their preparation and use Expired GB919720A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US829211A US3183054A (en) 1959-07-24 1959-07-24 Aldehyde condensation products and their use in treating fibrous materials
US3988A US3080281A (en) 1959-07-24 1960-01-22 Hydroxy-containing hemi-acetals, their preparation and use

Publications (1)

Publication Number Publication Date
GB919720A true GB919720A (en) 1963-02-27

Family

ID=26672451

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25593/60A Expired GB919720A (en) 1959-07-24 1960-07-22 Hemi-acetals, their preparation and use

Country Status (6)

Country Link
US (2) US3183054A (en)
BE (1) BE593301A (en)
CH (1) CH433226A (en)
ES (1) ES259814A1 (en)
GB (1) GB919720A (en)
MY (1) MY6400130A (en)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE593301A (en) * 1959-07-24
BE617614A (en) * 1961-05-18
US3189403A (en) * 1963-06-19 1965-06-15 Windus Wallace Tanning with a hemiacetal and resorcinol or pyrogallol solution
DE1233817B (en) * 1963-10-03 1967-02-09 Pfersee Chem Fab Process for the finishing of textile materials that contain natural and / or regenerated cellulose fibers
US3441367A (en) * 1965-12-22 1969-04-29 Us Agriculture Method for setting finishes on cellulosic textiles with catalyst composition of magnesium halide and organic acid
US3443987A (en) * 1965-12-29 1969-05-13 Shell Oil Co Process for treating fibrous material with aldehyde condensation products and the resulting material
US3535141A (en) * 1967-04-17 1970-10-20 Deering Milliken Res Corp Process for making sail release synthetic textile
US3645667A (en) * 1970-05-22 1972-02-29 Us Agriculture Nonaqueous cross linking of cellulose with a methylolated urea in the absence of an acidic catalyst
US4210755A (en) * 1970-12-24 1980-07-01 L'oreal Aminated γ-dialdehyde; methods for preparing the same and cosmetic compositions containing the same
US4014990A (en) * 1970-12-24 1977-03-29 Societe Anonyme Dite: L'oreal Animated-γ-dialdehydes in hair strengthening compositions
AR196921A1 (en) * 1972-04-01 1974-02-28 Basf Ag PROCEDURE FOR OBTAINING CURTIENT FORMULATIONS
US3867198A (en) * 1973-06-13 1975-02-18 Formica Corp Method of cleaning the surface of a decorative plastic laminate
US4167500A (en) * 1976-06-14 1979-09-11 Lord Corporation Aqueous compositions comprising phenolic resin and crosslinking agent
US4447241A (en) * 1982-04-12 1984-05-08 Springs Industries, Inc. Oxidative afterwash treatment for crease resisting fabrics
US4508594A (en) * 1984-06-28 1985-04-02 Nalco Chemical Company Polyaldehyde/polyacetal compositions
DE3811267C1 (en) * 1988-04-02 1989-05-18 Schill & Seilacher Gmbh & Co, 7030 Boeblingen, De
ATE126556T1 (en) 1990-02-01 1995-09-15 James River Corp ELASTIC, VOLUMINOUS FIBER OBTAINED BY CROSSLINKING WOOD FIBERS WITH POLYCARBONIC ACIDS.
DE4102545A1 (en) * 1991-01-29 1992-07-30 Basf Ag METHOD FOR GELING, PRELIMINATING AND GIVING BARE AND FUR BLOSSES AND FOR LEAVING LEATHER AND FUR
TW223103B (en) * 1992-02-03 1994-05-01 Ciba Geigy Ag
WO1999055784A1 (en) 1998-04-28 1999-11-04 Penford Corporation Novel sizing compounds
CN100357453C (en) * 2002-05-07 2007-12-26 巴斯福股份公司 Tanning agent and curing agent based on dialdehydes
DE102017123020A1 (en) * 2017-10-04 2019-04-04 Tfl Ledertechnik Gmbh Composition and method of tanning

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2078534A (en) * 1935-05-25 1937-04-27 Shell Dev Cyclic acetals and process for producing same
IT381105A (en) * 1939-03-04
US2696477A (en) * 1951-04-21 1954-12-07 Dan River Mills Inc Acrolein-formaldehyde condensation product
US2771337A (en) * 1952-05-03 1956-11-20 Dan River Mills Inc Acrolein-formaldehyde condensation products and process of applying the same to cellulose fabric
BE534687A (en) * 1954-01-08
BE593301A (en) * 1959-07-24

Also Published As

Publication number Publication date
BE593301A (en)
US3080281A (en) 1963-03-05
ES259814A1 (en) 1960-12-16
MY6400130A (en) 1964-12-31
CH433226A (en) 1967-04-15
US3183054A (en) 1965-05-11

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